Triphenylphosphine → 6-cyclobutyl-3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,3-triazolo[1,5-alpha]pyrimidine

HRID 1250178Notes

Reaction equation

HRID 1250178 reaction equation
[CH:1]1([C:5]2[C:6](=[O:21])[NH:7][C:8]3[N:9]([N:11]=[N:12][C:13]=3[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[CH:10]=2)[CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:41][N:42]1[C:46]([CH2:47]O)=[N:45][CH:44]=[N:43]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]1([C:5]2[C:6]([O:21][CH2:47][C:46]3[N:42]([CH3:41])[N:43]=[CH:44][N:45]=3)=[N:7][C:8]3[N:9]([N:11]=[N:12][C:13]=3[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[CH:10]=2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 178518574HCID 178518574, compound

Product 1

HCID 544292686-cyclobutyl-3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,3-triazolo[1,5-alpha]pyrimidineYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Cyclobutyl-3-(2-fluorophenyl)-4H-1,2,3-triazolo[1,5-α]pyrimidin-5-one (33 mg, 0.12 mmol), triphenylphosphine (76 mg, 0.29 mmol) and (2-methyl-2H-1,2,4-triazol-3-yl)methanol (37 mg, 0.29 mmol) were dissolved in dry tetrahydrofuran (1.5 ml) with stirring. Diethyl azodicarboxylate (46μl, 0.29 mmol) was added and the reaction stirred at room temperature for 16 hours before purification by preparative thin layer chromatography to afford 6-cyclobutyl-3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,3-triazolo[1,5-α]pyrimidine (31 mg, 70%) as a white crystalline solid, m.p. 181-184° C.; δH (400 MHz, d6-DMSO) 1.77-1.85 (1H, m, CH(CH2)3), 1.96-2.06 (1H, m, CH(CH2)3), 2.19-2.30 (4H, m, CH(CH2)3), 308 (1H, quintet, J=8.6 Hz, CH(CH2)3), 3.88 (3H, s, NMe, 5.65 (2H, s, OCH2), 7.34-7.38 (2H, m, ArH), 7.41-7.48 (1H, m, ArH), 7.94 (1H, s, triazole CH), 7.97 (1H, t, J=7.2 Hz, ArH), 9.25 (1H, s, pyrimidine CH); m/z (ES+) 380 (M+H+).

Workup

  1. stirringthe reaction stirred at room temperature for 16 hours before purification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-65d87cdc3c78479b9e90412aa7673ff2
Source dataset
uspto-grants-2002_01
Patent number
US06337331B1

Reaction notes

Loading…